IMAGINE

I had a conversation yesterday that I haven't been able to stop thinking about.

 She's at the top of her field. Literally running the organization. A woman in a space that was built by, and for, men. And she told me about a friend of hers who is anti-DEI and who pointed to her -- to her success, her title, her career -- as proof that DEI measures aren't necessary. You can get to the top without them, this friend said. So obviously it can be done.

Her response? "Now just imagine what I could have done if I didn't have all of the barriers in my way. The bias, the policies, the frat boy culture. IMAGINE."

Okay. Let's imagine.

Women can make it to the top in current conditions. That's why you see a few of them there. Right now, women account for 11% of Fortune 500 CEOs. That's 55 women, for the non-math girlies. Fifty-five, out of 500.

Now. IMAGINE how many women we would see if we removed not even all of the barriers. Let's not even dream that big. Let's start with HALF. Just half the barriers women face. Gone. How many women would we see?

 IMAGINE.

Now imagine ALL the barriers gone. How many women would we see in power? How different would our world look? How different would YOUR life look?

IMAGINE.

Okay so here's the thing though.

This is a systemic problem. You've probably heard that phrase before, and maybe it landed, or maybe it sounded like the kind of thing someone says before asking you to join a committee. So let me actually explain what it means and why it matters.

A systemic problem is one baked into the structure itself. And because it lives in the structure, you can't fix it by fixing individuals. You have to fix the system. Which means all the confidence training and networking workshops and "here's how to ask for a raise" advice in the world will not move the needle on its own, because it's aimed at the wrong place entirely. 

To see what I mean, let's take one of my favorite hobbies: warehouse sale shopping. I never really did this until I moved to Vancouver and discovered the Aritzia warehouse sale, which is complete mayhem, by the way. I have never seen lines like this in my life. But stay with me, because this sale is about to explain everything.

Imagine two groups of shoppers. Group 1 gets an invite that lets them shop the sale two days early. They also get a detailed map of the entire floor -- what's where, what everything costs, where the best pieces are sitting. They have unlimited time to browse. And they each get a personal stylist who walks through the sale with them, pulling pieces, flagging what works for their body, their style, their life. They leave with full bags and zero stress.

 Group 2 gets none of that. They show up two days later, no map, no stylist, no heads up. They walk into a floor that Group 1 has already picked through, dug through, and walked out of. A few people in Group 2 are really good at this. They know how to move fast, spot what's left, make something work. And we point to them and say "see, the sale is fair. People are figuring it out." But the large majority of group 2, walk out without finding any great bargains or pieces they really love. 

 And  yet, nobody goes back to consider how the different invites impacted the success of the shoppers.

 Instead, we started offering Group 2 workshops. How to shop faster. How to spot a good piece on a picked-over rack. How to network your way into better sale intel. And look, some of those tips are genuinely useful. But here's what none of them do: they don't change who got the invite. They don't put the good pieces back on the rack. And every time we offer another workshop instead of asking why the two groups had such a different experience, we're quietly agreeing that the setup was fine.

 The setup was not fine.

 That's exactly what's been happening to women in leadership for decades. The structure was built without them in mind, it keeps producing the same results, and the response has been to offer women better workshops. More confidence training. More networking tips. More advice on how to dig through the picked-over racks. All of it aimed at the wrong component entirely. Because the women were never the broken part.

And THAT is why the work I'm doing with my clients is bigger than just "giving women more confidence." 

Because frankly? Women don't need more confidence. The women I work with sometimes have a little doubt because they keep running into walls and ceilings that shouldn't be there. 

And look, hitting a wall that shouldn't exist will obviously make anyone question themselves for a second (I talked about my own experience with this in last week's newsletter). 

But overall? They have the confidence. They know they can do it. And they keep going because of it. What they ACTUALLY need is for the system to get the f*ck out of their way so they can build the best career for themselves, in whatever form that may take, IMAGINABLE.

Which means the work has to happen on two fronts simultaneously. Supporting women in navigating the structure as it exists right now, while also pushing hard on the structure itself. One without the other is simply not enough.

On one side, I work directly with women through Like a Leader -- a coaching and community experience built around my Painted Wolf Leadership Framework. Five cognitive skills that close the gap between how capable you are and how much of that actually lands in the room. Because here's the reality: the system was supposed to develop you, sponsor you, open doors for you. And for a lot of women, it just... didn't. Like a Leader exists to fill that gap. The goal isn't to teach you to navigate a picked-over rack better. The goal is to help you spot exactly what's going on, understand the structure you're working within, and build a path forward on your own terms while we work on the other side of this together.

And the other side? Fixing the invite list. Through my research, my book Painted Wolves, organizational consulting, keynote speaking, and book clubs and group events, I work with organizations and leaders to actually change the structure. The talks that challenge how we think about who gets to lead. The partnerships that push organizations to look hard at their own invite lists. The research that keeps building the evidence base for why this matters and what to do about it.

Two sides. Same mission. Because confidence-workshopping our way around a sh*tty system was obviously not going to work, and we all know it.

 Ready to be part of it?

 xoxo,

Kelsey

This Week's Thing: 

Grab a coffee, open your notes app, whatever works for you. And answer this: if the barriers were gone (the bias, the politics, the frat boy culture, the committee of a**holes living rent free in your head ) what would you go for? 

Not the practical version. Not the "realistic given my current situation" version. The real one. The IMAGINE version. 

What does your career look like? What are you building? What are you running? What are you finally saying out loud? 

Write it down. All of it. Keep it where you can see it and let it be your north star. Your reminder of what's possible, for you and for every woman who comes after you.

And if you're ready for support in making that a reality, that's what I specialize in 😘